WO1986001209A2 - NOUVEAUX PEPTIDES DE p-PHENYLENEDIAMINE ET REACTIFS LES CONTENANT POUR DETERMINER DES PROTEINASES DU SYSTEME DE COAGULATION DU SANG - Google Patents

NOUVEAUX PEPTIDES DE p-PHENYLENEDIAMINE ET REACTIFS LES CONTENANT POUR DETERMINER DES PROTEINASES DU SYSTEME DE COAGULATION DU SANG Download PDF

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Publication number
WO1986001209A2
WO1986001209A2 PCT/EP1985/000385 EP8500385W WO8601209A2 WO 1986001209 A2 WO1986001209 A2 WO 1986001209A2 EP 8500385 W EP8500385 W EP 8500385W WO 8601209 A2 WO8601209 A2 WO 8601209A2
Authority
WO
WIPO (PCT)
Prior art keywords
compound according
group
proteases
amino acid
compound
Prior art date
Application number
PCT/EP1985/000385
Other languages
German (de)
English (en)
Other versions
WO1986001209A3 (fr
Inventor
Knut Bartl
Udo Becker
Herbert Von Der Eltz
Helmut Lill
Hans-Georg Batz
Original Assignee
Boehringer Mannheim Gmbh
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Boehringer Mannheim Gmbh filed Critical Boehringer Mannheim Gmbh
Publication of WO1986001209A2 publication Critical patent/WO1986001209A2/fr
Publication of WO1986001209A3 publication Critical patent/WO1986001209A3/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
    • C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
    • C12Q1/56—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving blood clotting factors, e.g. involving thrombin, thromboplastin, fibrinogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • C07K14/665—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans derived from pro-opiomelanocortin, pro-enkephalin or pro-dynorphin
    • C07K14/675—Beta-endorphins
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/08—Tripeptides
    • C07K5/0802—Tripeptides with the first amino acid being neutral
    • C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
    • C07K5/0806—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atoms, i.e. Gly, Ala
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/08—Tripeptides
    • C07K5/0802—Tripeptides with the first amino acid being neutral
    • C07K5/0812—Tripeptides with the first amino acid being neutral and aromatic or cycloaliphatic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/10—Tetrapeptides
    • C07K5/1002—Tetrapeptides with the first amino acid being neutral
    • C07K5/1005—Tetrapeptides with the first amino acid being neutral and aliphatic
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
    • C12Q2337/00—N-linked chromogens for determinations of peptidases and proteinases
    • C12Q2337/10—Anilides
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N2333/00—Assays involving biological materials from specific organisms or of a specific nature
    • G01N2333/435—Assays involving biological materials from specific organisms or of a specific nature from animals; from humans
    • G01N2333/745—Assays involving non-enzymic blood coagulation factors
    • G01N2333/755—Factors VIII, e.g. factor VIII C [AHF], factor VIII Ag [VWF]

Definitions

  • X is an N-terminal amino acid protecting group
  • the alkyl groups in the above compounds have up to 6, preferably 1 to 3, carbon atoms.
  • the methyl group and ethyl group are particularly preferred.
  • Another object of the invention is a reagent for determining the proteases of the blood coagulation system, which is characterized in that it contains a compound according to formula 1, an oxidizing agent, an aniline or phenol derivative which forms a dye with phenylenediamine and buffer.
  • Solution 1 10 ml Tris-HCl buffer, pH 8.1 are mixed with 4 ml thromboplastin (Boehringer Mannheim, Order No. 244252) and 1 ml substrate solution (6.83 mmol / l in water) and then 1:10 with a Tris buffer pH 8.1, which additionally contains 6 mmol / l CaCl 2 and 0.25 mol / l urea.
  • Solution 2 10 ml Tris-HCl buffer, pH 8.1 are mixed with 4 ml thromboplastin (Boehringer Mannheim, Order No. 244252) and 1 ml substrate solution (6.83 mmol / l in water) and then 1:10 with a Tris buffer pH 8.1, which additionally contains 6 mmol / l CaCl 2 and 0.25 mol / l urea.
  • Solution 2 10 ml Tris-HCl buffer, pH 8.1 are mixed with 4 ml thromboplastin (Boehringer Mannheim, Order No. 24

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Medicinal Chemistry (AREA)
  • Zoology (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Neurosurgery (AREA)
  • Toxicology (AREA)
  • Physics & Mathematics (AREA)
  • Analytical Chemistry (AREA)
  • Hematology (AREA)
  • Biotechnology (AREA)
  • Immunology (AREA)
  • Microbiology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)

Abstract

Dans de nouvelles compositions ayant la formule générale (I), A est l'acide aminé arginine ou lysine, X est un groupe d'acides aminés de protection à terminal N ou un acide aminé D, Y est une liaison simple ou une chaîne composée de 1 à 3 acides aminés, NR1R2 est un groupe en position o ou p où R1 et R2 sont indépendants l'un de l'autre et représentent de l'hydrogène ou de l'alcoyle ayant 1 à 3 atomes C et R3 est un atome d'hydrogène, un groupe carboxyle, un atome d'halogène ou un groupe alcoyle ayant 1 à 3 atomes C. Ces compositions sont utiles comme substrats chromogènes de protéinases. Elles sont obtenues par réduction et le cas échéant par alkylation des nitroanilides correspondantes. Un réactif correspondant pour déterminer des protéïnases du système de coagulation du sang comprend une composition ayant la formule (I), un agent d'oxydation, un dérivé d'aniline ou de phénol qui forme un colorant par oxydation avec de la phénylène-diamine et une substance tampon.
PCT/EP1985/000385 1984-08-02 1985-07-31 NOUVEAUX PEPTIDES DE p-PHENYLENEDIAMINE ET REACTIFS LES CONTENANT POUR DETERMINER DES PROTEINASES DU SYSTEME DE COAGULATION DU SANG WO1986001209A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP3428543.1 1984-08-02
DE19843428543 DE3428543A1 (de) 1984-08-02 1984-08-02 Neue p-phenylendiamin-peptide und diese enthaltende reagenzien zur bestimmung von proteasen des blutgerinnungssystems

Publications (2)

Publication Number Publication Date
WO1986001209A2 true WO1986001209A2 (fr) 1986-02-27
WO1986001209A3 WO1986001209A3 (fr) 1986-03-27

Family

ID=6242223

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1985/000385 WO1986001209A2 (fr) 1984-08-02 1985-07-31 NOUVEAUX PEPTIDES DE p-PHENYLENEDIAMINE ET REACTIFS LES CONTENANT POUR DETERMINER DES PROTEINASES DU SYSTEME DE COAGULATION DU SANG

Country Status (6)

Country Link
EP (1) EP0190299A1 (fr)
JP (1) JPS61501635A (fr)
AU (1) AU564556B2 (fr)
DE (1) DE3428543A1 (fr)
WO (1) WO1986001209A2 (fr)
ZA (1) ZA855814B (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4797472A (en) * 1986-03-21 1989-01-10 Kabivitrum Ab New peptide derivatives
FR2644697A1 (fr) * 1989-03-24 1990-09-28 Poudres & Explosifs Ste Nale Composes anesthesiques a duree d'action controlee et compositions pharmaceutiques les contenant
WO1996021740A1 (fr) * 1995-01-10 1996-07-18 Hendrik Coenraad Hemker Procedes pour la determination du potentiel thrombine endogene (etp), et substrats pour thrombine utilises dans ces procedes
WO2006040037A1 (fr) 2004-10-12 2006-04-20 F. Hoffmann-La Roche Ag Synthese de peptides en phase solide

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4717658A (en) * 1985-12-03 1988-01-05 Miles Inc. Gram negative bacteria screening method with horseshoe crab amebocyte lysate (LAL)
FI860043A (fi) * 1986-01-06 1987-07-07 Orion Yhtymae Oy Peptidsubstrat samt foerfarande foer kvantitativ analys av endotoxin.
SE8601327D0 (sv) * 1986-03-21 1986-03-21 Kabivitrum Ab Nya peptidderivat
EP1157029B1 (fr) 1999-02-23 2005-12-28 Pentapharm AG Derives d'oligopeptides pour la mesure electrochimique de l'activite de proteases

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0056210A2 (fr) * 1981-01-09 1982-07-21 Centre National De La Recherche Scientifique (Cnrs) Procédé pour le dosage fluorimétrique des endotoxines, nouveaux peptides portant un fluorophore utilisables dans ledit procédé et leur méthode de préparation
JPS57176940A (en) * 1981-04-25 1982-10-30 Wako Pure Chem Ind Ltd Novel color-developing peptide derivative
JPS58172354A (ja) * 1982-04-05 1983-10-11 Dai Ichi Pure Chem Co Ltd ペプチド誘導体
GB2118190A (en) * 1982-04-13 1983-10-26 Erba Farmitalia Peptides with sauvagine-like activity
EP0110306A2 (fr) * 1982-11-27 1984-06-13 BEHRINGWERKE Aktiengesellschaft Composés chromogènes, leur procédé d'obtention et leur emploi
JPH08142597A (ja) * 1994-11-21 1996-06-04 Dainippon Printing Co Ltd 転写箔及びこれを用いた装飾ガラス

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0056210A2 (fr) * 1981-01-09 1982-07-21 Centre National De La Recherche Scientifique (Cnrs) Procédé pour le dosage fluorimétrique des endotoxines, nouveaux peptides portant un fluorophore utilisables dans ledit procédé et leur méthode de préparation
JPS57176940A (en) * 1981-04-25 1982-10-30 Wako Pure Chem Ind Ltd Novel color-developing peptide derivative
JPS58172354A (ja) * 1982-04-05 1983-10-11 Dai Ichi Pure Chem Co Ltd ペプチド誘導体
GB2118190A (en) * 1982-04-13 1983-10-26 Erba Farmitalia Peptides with sauvagine-like activity
EP0110306A2 (fr) * 1982-11-27 1984-06-13 BEHRINGWERKE Aktiengesellschaft Composés chromogènes, leur procédé d'obtention et leur emploi
JPH08142597A (ja) * 1994-11-21 1996-06-04 Dainippon Printing Co Ltd 転写箔及びこれを用いた装飾ガラス

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, Vol. 100, 1984 Columbus, Ohio (US) see page 645, Abstract 121624y & JP, A, 58172354 (Daiichi Kagaku Takuhin K.K.) 11 October 1983 *
CHEMICAL ABSTRACTS, Vol. 95, 1981 Columbus, Ohio (US) see page 201, Abstract 109987q & JP, A, 8142597 (Seikagaku Kogyo Co. Ltd.) 20 April 1981 *
CHEMICAL ABSTRACTS, Vol. 98, 1983, Columbus, Ohio (US) see page 554, Abstract 161166x & JP, A, 57176940 (Wako Pure Chemical Industries Ltd.) 30 October 1982 *
CHEMICAL ABSTRCTS, Vol. 99, 1983 Columbus, Ohio (US) see page 697, Abstract 122953c & JP, a, 5890535 (Wako Pure Chemical Industries, Ltd.) 30 May 1983 *
Journal of Medicinal Chemistry, Vol. 268 No. 5, May 1983 The American Chemical Society (US) P.K. CHAKRAVARTY et al.: "Plasmin-Activated Prodrugs for Cancer Chemotherapy, 1. Synthesis and Biological Activity of Peptidylacivicin and Peptidylphenylenediamine Mustard", pages 633-638, see the whole article *

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4797472A (en) * 1986-03-21 1989-01-10 Kabivitrum Ab New peptide derivatives
FR2644697A1 (fr) * 1989-03-24 1990-09-28 Poudres & Explosifs Ste Nale Composes anesthesiques a duree d'action controlee et compositions pharmaceutiques les contenant
WO1990011292A2 (fr) * 1989-03-24 1990-10-04 Societe Nationale Des Poudres Et Explosifs Composes anesthesiques a duree d'action controlee et compositions pharmaceutiques les contenant
WO1990011292A3 (fr) * 1989-03-24 1990-11-15 Poudres & Explosifs Ste Nale Composes anesthesiques a duree d'action controlee et compositions pharmaceutiques les contenant
WO1996021740A1 (fr) * 1995-01-10 1996-07-18 Hendrik Coenraad Hemker Procedes pour la determination du potentiel thrombine endogene (etp), et substrats pour thrombine utilises dans ces procedes
US6207399B1 (en) 1995-01-10 2001-03-27 Hendrik Coenraad Hemker Methods of determining endogenous thrombin potential (ETP) and thrombin substrates for use in said methods
WO2006040037A1 (fr) 2004-10-12 2006-04-20 F. Hoffmann-La Roche Ag Synthese de peptides en phase solide
KR100920297B1 (ko) * 2004-10-12 2009-10-08 에프. 호프만-라 로슈 아게 고상 펩티드 합성 방법

Also Published As

Publication number Publication date
WO1986001209A3 (fr) 1986-03-27
AU564556B2 (en) 1987-08-13
EP0190299A1 (fr) 1986-08-13
JPS61501635A (ja) 1986-08-07
AU4723885A (en) 1986-03-07
DE3428543A1 (de) 1986-02-13
ZA855814B (en) 1986-04-30

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